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Triphenylphosphine → ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235950
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HRID 2235950 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12])[C:5]([CH3:14])=[CH:4][N:3]=1.[CH2:15]([O:17][C:18](=[O:30])[CH2:19][C@H:20]1[C:28]2[C:23](=[CH:24][C:25](O)=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH3:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[CH2:9][CH2:10][CH2:11][O:12][C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[C@H:20]([CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:30])[CH2:21][CH2:22]3)[C:5]([CH3:14])=[CH:4][N:3]=1
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참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 730421,1'-(Azodicarbonyl)dipiperidine2회HCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 593004673-[(2-Chloro-5-methyl-4-pyrimidinyl)(methyl)amino]-1-propanol

생성물 1

HCID 59300440ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate
수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]-1-propanol (Example 341, 785 mg, 3.64 mmol) and ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 401 mg, 1.82 mmol) in THF (17 mL) were added PPh3 (954 mg, 3.64 mmol) and ADDP (918 mg, 3.64 mmol). The reaction mixture was vigorously stirred at rt for 24 h after which additional PPh3 (954 mg, 3.64 mmol) and ADDP (918 mg, 3.64 mmol) were added. After an additional 24 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (3:1 hexanes/EtOAc) to give the product (586 mg, 77%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.26 (t, 3H), 1.71-1.76 (m, 1H), 2.06-2.11 (m, 2H), 2.26 (s, 3H), 2.34-2.42 (m, 2H), 2.67-2.88 (m, 3H), 3.15 (s, 3H), 3.49-3.50 (m, 1H), 3.70 (t, 2H), 3.94 (t, 2H), 4.13 (q, 2H), 6.64 (d, 1 H), 6.70 (s, 1H), 7.02 (d, 1H), 7.75 (s, 1H).

후처리

  1. additionwere added
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (3:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-27277c552f6e4bee8d2182db36390fb4
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714004B2

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